31301-30-1

Usage

Uses

Used in Coordination Complex Synthesis:
1,10-Phenanthroline-4-carboxaldehyde is used as a building block for the synthesis of coordination complexes, leveraging its ability to chelate metal ions, which is crucial for the formation of stable complexes with various applications in different fields.
Used in Metal Chelation:
As a metal chelator, 1,10-Phenanthroline-4-carboxaldehyde is employed to bind metal ions, which is significant in various chemical and biological processes, including the stabilization of metalloenzymes and the development of metal-based drugs.
Used in Fluorescence Quenching Studies:
1,10-Phenanthroline-4-carboxaldehyde is utilized in fluorescence quenching studies, where its interaction with fluorophores can lead to the reduction of fluorescence, a phenomenon that is valuable for understanding molecular interactions and developing new analytical methods.
Used in Analytical Chemistry:
In the field of analytical chemistry, 1,10-Phenanthroline-4-carboxaldehyde serves as a reagent for the determination of metal ions. Its ability to form complexes with these ions aids in their detection and quantification, which is essential for environmental monitoring and material characterization.
Used in Medicine:
1,10-Phenanthroline-4-carboxaldehyde has been studied for its potential application in medicine, where it may contribute to the development of new drugs or therapeutic agents, particularly those involving metal ion interactions.
Used in Materials Science:
In materials science, 1,10-Phenanthroline-4-carboxaldehyde is explored for its potential to enhance or modify the properties of materials, such as improving the stability or reactivity of certain compounds in various applications.
Used in Catalysis:
1,10-Phenanthroline-4-carboxaldehyde is also considered for use in catalysis, where it may act as a catalyst or a catalyst support, facilitating chemical reactions with enhanced efficiency and selectivity.

Upstream product

• 31301-28-7 4-methyl-1,10-phenanthroline 

Downstream Products

• 31301-27-6 1,10-phenanthroline-4-carboxylic acid 
• 1345842-95-6 4-(di(2-picolyl)aminomethyl)-1,10-phenanthroline 
• 184946-30-3 (1,10-phenanthroline-4-yl)methanol 

Relevant academic research and scientific papers

Dinuclear PhotoCORMs: Dioxygen-Assisted Carbon Monoxide Uncaging from Long-Wavelength-Absorbing Metal-Metal-Bonded Carbonyl Complexes

We describe a new strategy for triggering the photochemical release of caged carbon monoxide (CO) in aerobic media using long-wavelength visible and near-infrared (NIR) light. The dinuclear rhenium-manganese carbonyl complexes (CO)5ReMn(CO)3(L), where L = phenanthroline (1), bipyridine (2), biquinoline (3), or phenanthrolinecarboxaldehyde (4), each show a strong metal-metal-bond-to-ligand (σMM → πL*) charge-transfer absorption band at longer wavelengths. Photolysis with deep-red (1 and 2) or NIR (3 and 4) light leads to homolytic cleavage of the Re-Mn bonds to give mononuclear metal radicals. In the absence of trapping agents, these radicals primarily recombine to reform dinuclear complexes. In oxygenated media, however, the radicals react with dioxygen to form species much more labile toward CO release via secondary thermal and/or photochemical reactions. Conjugation of 4, with an amine-terminated poly(ethylene glycol) oligomer, gives a water-soluble derivative with similar photochemistry. In this context, we discuss the potential applications of these dinuclear complexes as visible/NIR-light-photoactivated CO-releasing moieties (photoCORMs).

Cu(ii) templated formation of [: N] pseudorotaxanes (n = 2, 3, 4) using a tris-amino ether macrocyclic wheel and multidentate axles

A tris-amine and oxy-ether functionalised macrocyclic wheel (NaphMC) and various phenanthroline based multidentate axles (L1, L2 and L3) are utilised for the formation of [n]pseudorotaxanes (n = 2, 3, 4) in high yields via Cu(ii) temptation and π-π stacking interactions. The systematic development of threaded supramolecular architectures i.e. [2]pseudorotaxane {[2]CuPR(ClO4)2}, [3]pseudorotaxane {[3]CuPR(ClO4)4} and [4]pseudorotaxane {[4]CuPR(ClO4)6} from bidentate L1, linear tetradentate L2 and tripodal hexadentate L3 respectively is described. All the [n]pseudorotaxanes are well characterized by several spectroscopy and other experimental techniques such as electrospray ionization mass spectrometry (ESI-MS), isothermal titration calorimetric (ITC) study, UV/Vis, EPR, IR and elemental analysis. Moreover, the single crystal X-ray analysis of [2]pseudorotaxane confirmed the threading of L1 in the cavity of NaphMC, resulting in the formation of a penta-coordinated Cu(ii) ternary complex. ITC studies revealed the order of binding constant values for the formation of [n]pseudorotaxanes from the NaphMC-Cu(ii) complex and multidentate axles as L3 > L2 > L1. Finally, we have also shown the ability of Ni(ii) to act as a metal template in the formation of [n]pseudorotaxanes.

Phenanthroline—A Versatile Ligand for Advanced Functional Polymeric Materials

The controlled incorporation of phenanthroline moieties into polymers is introduced, demonstrating their application as metal-ion complexing ligands for the construction of advanced macromolecular structures. Specifically, two phenanthroline-containing monomers based on acrylate and styrene functionalities, were synthesized. Each monomer was readily copolymerized with either N,N-dimethylacrylamide or styrene via nitroxide-mediated polymerization, resulting in narrowly distributed polar or non-polar copolymers. To demonstrate the versatility of the established polymer systems, the polar polymer was employed for transition metal induced single-chain nanoparticle formation, verified by diffusion-ordered NMR and UV/Vis spectroscopy. Furthermore, the non-polar polymer allows facile incorporation of lanthanide ions, creating luminescent metallo-polymers, in-depth characterized by advanced photophysical experiments and 2D NMR measurements.

A green-emitting iridium complex used for sensitizing europium ion with high quantum yield

A green-emitting iridium(III) complex Ir(dfppy)2(cbphen) (dfppy?=?2-(4′,6′-difluoro-phenyl)pyridine, cbphen?=?4-carboxylate-phenanthroline) was synthesized and fully characterized. The single crystal data confirm its Ir(C^N)2(N^N) structure with the carboxylate group on phenanthroline stretching freely which could be able to combine with europium(III) ion. The complex was reacted with EuCl3·6H2O and Eu(TTA)3·2H2O to provide bimetallic complexes. Through photophysical studies, characteristic emission from EuIIIion was obtained, and meanwhile the green emission from iridium(III) center was almost quenched completely, suggesting this iridium(III) complex is a good sensitizer for EuIIIions. It is well worth noticing that by introducing the iridium(III) complex as a chromophore, the excitation wavelength of EuIIIion has been extended to the visible range (470?nm). Besides, due to the efficient energy transfer, the quantum yield of Ir3-Eu was nearly equal to that of Eu(TTA)3·2H2O.

Synthetic control over photoinduced electron transfer in phosphorescence zinc sensors

Despite the promising photofunctionalities, phosphorescent probes have been examined only to a limited extent, and the molecular features that provide convenient handles for controlling the phosphorescence response have yet to be identified. We synthesized a series of phosphorescence zinc sensors based on a cyclometalated heteroleptic Ir(III) complex. The sensor construct includes two anionic cyclometalating ligands and a neutral diimine ligand that tethers a di(2-picolyl)amine (DPA) zinc receptor. A series of cyclometalating ligands with a range of electron densities and band gap energies were used to create phosphorescence sensors. The sensor series was characterized by variable-temperature steady-state and transient photoluminescence spectroscopy studies, electrochemical measurements, and quantum chemical calculations based on time-dependent density functional theory. The studies demonstrated that the suppression of nonradiative photoinduced electron transfer (PeT) from DPA to the photoexcited IrIV species provided the underlying mechanism that governed the phosphorescent response to zinc ions. Importantly, the Coulombic barrier, which was located on either the cyclometalating ligand or the diimine ligand, negligibly influenced the PeT process. Phosphorescence modulation by PeT strictly obeyed the Rehm-Weller principle, and the process occurred in the Marcus-normal region. These findings provide important guidelines for improving sensing performance; an efficient phosphorescence sensor should include a cyclometalating ligand with a wide band gap energy and a deep oxidation potential. Finally, the actions of the sensor were demonstrated by visualizing the intracellular zinc ion distribution in HeLa cells using a confocal laser scanning microscope and a photoluminescence lifetime imaging microscope.

Phosphorescent sensor for biological mobile zinc

A new phosphorescent zinc sensor (ZIrF) was constructed, based on an Ir(III) complex bearing two 2-(2,4-difluorophenyl)pyridine (dfppy) cyclometalating ligands and a neutral 1,10-phenanthroline (phen) ligand. A zinc-specific di(2-picolyl)amine (DPA) receptor was introduced at the 4-position of the phen ligand via a methylene linker. The cationic Ir(III) complex exhibited dual phosphorescence bands in CH3CN solutions originating from blue and yellow emission of the dfppy and phen ligands, respectively. Zinc coordination selectively enhanced the latter, affording a phosphorescence ratiometric response. Electrochemical techniques, quantum chemical calculations, and steady-state and femtosecond spectroscopy were employed to establish a photophysical mechanism for this phosphorescence response. The studies revealed that zinc coordination perturbs nonemissive processes of photoinduced electron transfer and intraligand charge-transfer transition occurring between DPA and phen. ZIrF can detect zinc ions in a reversible and selective manner in buffered solution (pH 7.0, 25 mM PIPES) with Kd = 11 nM and pKa = 4.16. Enhanced signal-to-noise ratios were achieved by time-gated acquisition of long-lived phosphorescence signals. The sensor was applied to image biological free zinc ions in live A549 cells by confocal laser scanning microscopy. A fluorescence lifetime imaging microscope detected an increase in photoluminescence lifetime for zinc-treated A549 cells as compared to controls. ZIrF is the first successful phosphorescent sensor that detects zinc ions in biological samples.

Synthesis and characterization of nitroxide-linked ruthenium complexes as molecular probes for microheterogeneous environments

Several new TEMPO (2,2,6,6-tetramethylpiperidine N-oxide)-labeled ruthenium complexes were prepared. They can be discerned in two different classes featuring rigid and flexible linkers between the ruthenium(II)-polypyridyl complex and the stable nitroxide. The bis(heteroleptic) ruthenium complexes were synthesized from [Ru(L2)]Cl2 (L = 2,2'-bipyridine or 1,10-phenanthroline) and newly prepared phenanthroline-TEMPO-ligands. Finally, a tris(heteroleptic), spin-labeled ruthenium complex has been prepared from [Ru(DMSO)4]Cl2, dipyrido[3,2-a:2',3'-c]phenazine (dppz), 1,10-phenanthroline and a phenanthroline-TEMPO-ligand with a rigid linker.

Porphyrins meso-Substituted with Phenanthrene and 1,10-Phenanthroline

Meso-tetrakis(9-phenanthryl)porphyrin and meso-tetrakis(1,10-phenanthrolin-4-yl)porphyrin were obtained and characterized by spectroscopy methods.The porphyrin containing phenanthroline substituents was formed with much smaller yield.It showed much slower progress of metallation with Cu(I) and Zn(II)-ions than the phenanthreneporphyrin.While attachment of phenanthrene did not result in any meaningful changes in the uv vis spectrum when compared to other meso-substituted tetraarylporphyrins (except that of paracyclophanylporphyrin), the appearance of two N centers in each meso substituent substantially altered porphyrin absorption in the 530-600 nm region.Although the 1 H nmr 300 MHz spectra of both porphyrins showed the same deshielding of β-pyrrole protons, the shielding of NH protons was more advanced in phenanthrolineporphyrin.